Secondary Metabolism

Code:

Q3025

Acronym:

Q3025

Level:

300

Keywords
Classification	Keyword
OFICIAL	Chemistry

Instance: 2020/2021 - 1S

Active?	Yes
Responsible unit:	Chemistry
Course/CS Responsible:	Bachelor in Biochemistry

Cycles of Study/Courses

Acronym	No. of Students	Study Plan	Curricular Years	Credits UCN	Credits ECTS	Contact hours	Total Time
L:BQ	4	Official Study Plan	3	-	6	56	162

Teaching language

Portuguese

Objectives

This course fits in the basic formation of a biochemistry degree. 
The living organisms, plants, bacteria, fungi, liquens, insects, animals... all produce an impressive array of compounds, with very diverse structures, which have enormous importance not only to the producers but also to mankind and are an immense reservoir of chemical diversity. Within this perspective and with the goal of complementing the knowledge acquired in passed years, we intend that the students have a basic knowledge about the different biogenetic pathways (acetate, mevalonate, non-mevalonate, shikimate…) linked to the production of natural products, their evolution and regulation as well as their integration with the basic or primary metabolism. 
Following this premises our aims are that by the end of this course the students: 
-Understand the key biosynthetic pathways for the biosynthesis of natural products, 
-Recognise and be able to apply key biosynthetic reactions in order to predict how organisms make secondary metabolites, 
-Understand the biological significance of secondary metabolites, 
-Be able to work in natural product field, 
-Have a better understanding of how works the inter- and intra-species relationships and their ecological importance.

Learning outcomes and competences

 By the end of this course the student should be able of: 
-Understand the key biosynthetic pathways for the biosynthesis of natural products, 
-Recognise and apply key biosynthetic reactions in order to predict how organisms make secondary metabolites, 
-Understand the biological significance of secondary metabolites, 
- Understand how works the inter- and intra-species relationships and their ecological importance.

Working method

Presencial

Pre-requirements (prior knowledge) and co-requirements (common knowledge)

Are recommended pre-requisites basic knowledgement in General Chemistry, Physical Chemistry, Organic Chemistry and, above all, strutural Biochemistry.

Program

I – Secondary Metabolism Biosynthetic Pathways. 
1. Secondary Metabolites derived from Acetate – Polyketides (6 hours) 
1.1 – Relationship between Fatty Acids and Polyketides Biosynthetic Pathways. 
1.1.1 - Fatty Acid Synthases (FAS) versus Polyketide Synthases (PKS). 
1.1.2 - Processive and Iterative Type of Activity. 
1.1.3 - Macrolides: Erythromycin. 
1.2 – Polyphenolic Compounds Biosynthesis. 
1.2.1 - Cyclization of linear polyketides: Polyphenols Formation. 
1.2.2 - 4 C2 units: 6-Methylsalicilic acid (6-MSA) 
1.2.3 - 5 C2 units: Citrinine. 
1.2.4 - 6 C2 units: Naphthoquinones. 
1.2.5 - 7 C2 units. 
1.2.6 - 8 C2 units: Anthraquinones. 
1.2.1 - Phenolic Oxidative Coupling. Usnic Acid. 
1.3 – Oxidative Cleavage of Aromatic Rings. 
1.4 – Methodologies to Study the Secondary Metabolites Biosynthesis. 
2. Isoprenoids - Mevalonate and Non-Mevalonate Pathways (6 hours) 
2.1 - Isoprene Rule and Terpenoid Classification. 
2.2 – Mevalonate Pathway. Enzymes and their characteristics. 
2.3 - Non-Mevalonate Pathway. Enzimes and their characteristics. 
2.4 - IPP/DMAPP Isomerization. Diversity in the IPP/DMAPP Biosynthesis. 
2.5 - Different Terpene Classes Biosynthesis. Enzymes and their characteristics. 
2.5.1 – Hemiterpenes. 
2.5.2 – Monoterpenes. 
2.5.3 – Sesquiterpenes and Sesquiterpene Lactones. 
2.5.4 – Diterpenes. 
3. Shikimate Biosyntetic Pathway (4 hours) 
3.1 - Biosynthetic Pathway to Amino acids Phenylalanine and Tirosine. Enzymes, their reactions e characteristics. 
3.2 – Metabolites derivated from Phenylalanine. Enzymes, their reactions e characteristics. 
3.2.1 – Phenylpropanoids. 
3.2.2 – Lignins 
3.2.3 – Lignans 
3.2.4 – Coumarins 
3.3 – Mixed Biosyntetic pathway Shiquimate-Acetate. 
3.3.1 – Flavonoids 
3.3.2 – Xantones 
3.3.3 – Stilbenes 
4. Alkaloids Biosynthetic Pathways (3 hours) 
4.1 - Introduction 
4.2 – Alkaloids Derived from Metabolism of Ornithine and Lysine 
4.2.1 Pyrrolidine and Piperidine Alkaloids 
4.2.1.1 – Hyoscyamine and scopolamine 
4.2.1.2 – Cocaine 
4.2.2 - Pyrrolizidíne and Quinolizidíne Alkaloids 
4.2.3 – Pyridine Alkaloids 
4.3 – Alkaloids Derived from Metabolism of Phenylalanine and Tyrosine 
4.3.1 – Simple Monocyclic 
4.3.2 – Isoquinolines 
4.3.3 – Benzylisoquinolines and bis-benzylisoquinolines 
4.3.4 – Amaryllidaceae Alkaloids 
5. Nonribosomal Peptides (3 hours) 
5.1 - Nonribosomal Peptides vs ribosomal Peptides
5.2 - Nonribosomal Peptides biosythesis
5.3 - Types of NRPS;
5.4 - NRPS/PKS Hybrids
II – General Aspects from the Secondary Metabolism (4 hours) 
6. Primary and Secondary Metabolism 
6.1 - Introduction 
6.2 - Intermediary/Primary Metabolism 
6.3 - Secondary Metabolism 
7. Secondary Metabolites distinguishing characteristics 
7.1 – Structural Diversity 
7.2 – Accumulation of Secondary Metabolites 
8. Secondary Metabolism Enzymology 
8.1 – Plasticity of Reaction Pathways 
8.2 - Enzyme Efficiency 
8.3 – Enzyme Recruitment 
8.4 – Induction and Regulation 
9 - Shunt and Overflow Metabolism 
III - Teorical - Practical Classes 
10 - Strategies used to obtain Bioactive Natural Products. Isolation and Structural elucidation methods. 
11 - Exercise resolution about biosynthetic mechanisms in the different pathways. 
12 - Student Presentation of seminars according several themes such as: Ecological Biochemistry, Combinatorial Biosynthesis, Secondary Metabolites in Therapeutics.

Mandatory literature

Dewick Paul M.; Medicine natural products. ISBN: 978-0-470-74167-2

Complementary Bibliography

Ana M. Lobo, Ana M. Lourenço; Biossíntese de Produtos Naturais, IST Press. ISBN: ISBN: 978-972-8469-50-4
ULL; Natural Product Reports. ISBN: 0265-0568

Comments from the literature

Natural Product Reports, Royal Society of Chemistry (Selected Papers )

Teaching methods and learning activities

No início do semestre lectivo é apresentado aos alunos um programa sucinto calendarizado para as aulas teóricas, teórico-práticas e avaliações intercalares. 
Nas aulas teóricas é utilizado um sistema de projecção de diapositivos em Power Point utilizando computador e projector vídeo para apresentação formal da matéria. São disponibilizados aos alunos os diapositivos apresentados. Os alunos são incentivados a participarem com questões ou comentários durante as aulas 
Nas aulas teórico-práticas aborda-se a resolução de problemas biossintéticos, a apresentação de seminários e é feita uma abordagem aos produtos naturais, sua importância e estratégias de obtenção de Metabolitos Secundários Bioactivos.

Software

ACDLabs ChemSketch 2017

keywords

Physical sciences > Chemistry > Biochemistry > Metabolism
Physical sciences > Chemistry > Biochemistry

Evaluation Type

Distributed evaluation with final exam

Assessment Components

Designation	Weight (%)
Exame	100,00
Total:	100,00

Amount of time allocated to each course unit

Designation	Time (hours)
Frequência das aulas	100,00
Total:	100,00

Eligibility for exams

According with the current regulations.

Calculation formula of final grade

Students are allowed to choose whether they wish to be evaluated through a single final exam or via two parcial exams. 
For those who have chosen to be evaluated though a single final exam, their grade will be the grade obtained in this exam. 
For those who have chosen to be evaluated via two parcial exams their grade will be the average of these two exams. 

Examinations or Special Assignments

Are not provided

Special assessment (TE, DA, ...)

According with the current regulations.

Classification improvement

According with the current regulations.

Observations

Are recommended as pre-requisites basic knowledgement in General Chemistry, Physical Chemistry, Organic Chemistry and, above all, strutural Biochemistry.